224294-26-2Relevant articles and documents
Functionalization of the chalcone scaffold for the discovery of novel lead compounds targeting fungal infections
Bonvicini, Francesca,Gentilomi, Giovanna A.,Bressan, Francesca,Gobbi, Silvia,Rampa, Angela,Bisi, Alessandra,Belluti, Federica
, (2019)
The occurrence of invasive fungal infections represents a substantial threat to human health that is particularly serious in immunocompromised patients. The limited number of antifungal agents, devoid of unwanted toxic effects, has resulted in an increased demand for new drugs. Herein, the chalcone framework was functionalized to develop new antifungal agents able to interfere with cell growth and with the infection process. Thus, a small library of chalcone-based analogues was evaluated in vitro against C. albicans ATCC 10231 and a number of compounds strongly inhibited yeast growth at non-cytotoxic concentrations. Among these, 5 and 7 interfered with the expression of two key virulence factors in C. albicans pathogenesis, namely, hyphae and biofilm formation, while 28 emerged as a potent and broad spectrum antifungal agent, enabling the inhibition of the tested Candida spp. and non-Candida species. Indeed, these compounds combine two modes of action by selectively interfering with growth and, as an added value, weakening microbial virulence. Overall, these compounds could be regarded as promising antifungal candidates worthy of deeper investigation. They also provide a chemical platform through which to perform an optimization process, addressed at improving potency and correcting liabilities.
Studies in crystal engineering: Steering ability of fluorine in 4- styrylcoumarins
Vishnumurthy, Kodumuru,Guru Row, Tayur N.,Venkatesan, Kailasam
, p. 4095 - 4108 (2007/10/03)
In continuation of our studies on crystal engineering using fluorine as a steering group, the photobehaviour of di and tri fluoro 4-styrylcoumarins has been examined. It is found that out of the five derivatives, four crystallize into β-packing mode producing syn-HH photodimer upon irradiation whereas the parent hydrocarbon produces an anti H-T dimer. The packing features of the photolabile crystals of 4-(4-fluorostyryl)-6-fluorocoumarin (1), 4-(2,6-difluorostyryl)-6-fluorocoumarin (2) and the photodimer (3a) of 4-(2,6-fluorostyryl)-7-fluorocoumarin (3) have been determined by single crystal X-ray diffraction studies. The stereochemistry of the photodimer of 4-(2-fluorostyryl)-6-fluorocoumarin (4) is deduced based on preliminary X- ray crystallographic data. However, 4-(2,6-difluorostyryl) coumarin (5) is photoinert. The remarkable steering ability of fluorine is established with the molecular packing in the crystal lattice leading to the formation of syn H-H dimer in the above four examples.
